EP2639216A4 - Halogenated indenones and method for producing optically active indanones or optically active indanols by using same - Google Patents

Halogenated indenones and method for producing optically active indanones or optically active indanols by using same

Info

Publication number
EP2639216A4
EP2639216A4 EP11839101.0A EP11839101A EP2639216A4 EP 2639216 A4 EP2639216 A4 EP 2639216A4 EP 11839101 A EP11839101 A EP 11839101A EP 2639216 A4 EP2639216 A4 EP 2639216A4
Authority
EP
European Patent Office
Prior art keywords
optically active
indenones
indanols
indanones
halogenated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP11839101.0A
Other languages
German (de)
French (fr)
Other versions
EP2639216B1 (en
EP2639216A1 (en
Inventor
Shohei Yamamoto
Masakatsu Nishihachijo
Rie Tanaka
Shigeru Kawano
Akio Fujii
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kaneka Corp
Original Assignee
Kaneka Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kaneka Corp filed Critical Kaneka Corp
Publication of EP2639216A1 publication Critical patent/EP2639216A1/en
Publication of EP2639216A4 publication Critical patent/EP2639216A4/en
Application granted granted Critical
Publication of EP2639216B1 publication Critical patent/EP2639216B1/en
Not-in-force legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26—Ketones
    • C12P7/38—Cyclopentanone- or cyclopentadione-containing products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP11839101.0A 2010-11-09 2011-11-08 Halogenated indenones and method for producing optically active indanones or optically active indanols by using same Not-in-force EP2639216B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010251095 2010-11-09
PCT/JP2011/075767 WO2012063843A1 (en) 2010-11-09 2011-11-08 Halogenated indenones and method for producing optically active indanones or optically active indanols by using same

Publications (3)

Publication Number Publication Date
EP2639216A1 EP2639216A1 (en) 2013-09-18
EP2639216A4 true EP2639216A4 (en) 2014-12-10
EP2639216B1 EP2639216B1 (en) 2018-07-11

Family

ID=46050984

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11839101.0A Not-in-force EP2639216B1 (en) 2010-11-09 2011-11-08 Halogenated indenones and method for producing optically active indanones or optically active indanols by using same

Country Status (5)

Country Link
EP (1) EP2639216B1 (en)
JP (2) JP5941410B2 (en)
CN (2) CN103209949B (en)
DK (1) DK2639216T3 (en)
WO (1) WO2012063843A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012176066A1 (en) 2011-06-20 2012-12-27 H. Lundbeck A/S Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia
AR094054A1 (en) 2012-12-19 2015-07-08 H Lundbeck As 6-CHLORINE-3- (FENIL-D₅) -INDEN-1-ONA AND USE OF THE SAME
CN106011094B (en) * 2016-07-27 2020-11-03 苏州汉酶生物技术有限公司 Engineered ketoreductase polypeptide and method for preparing (3R,5S) -6-chloro-3, 5-dyhydroxyl hexanoic acid tert-butyl ester by using same
US11535600B2 (en) 2018-12-03 2022-12-27 H. Lundbeck A/S Prodrugs of 4-((1R,3S)-6-chloro-3-phenyl-2,3-dihydro-1H-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1R,3S)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1H-inden-1-yl)-2,2-dimethyl-1-(methyl-d3)piperazine
CN111261786B (en) * 2020-01-19 2023-07-28 浙江大学 Efficient organic solar cell based on asymmetric end-capped electron acceptor

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK55192D0 (en) 1992-04-28 1992-04-28 Lundbeck & Co As H 1-piperazino-1,2-dihydroindene derivatives
JP3438890B2 (en) 1992-08-10 2003-08-18 鐘淵化学工業株式会社 DNA encoding decarbamylase with improved thermostability and use thereof
EP1116795B1 (en) 1999-07-21 2008-03-12 Kaneka Corporation Process for producing optically active pyridineethanol derivatives
CA2360376C (en) 1999-12-03 2005-04-26 Noriyuki Kizaki Novel carbonyl reductase, gene thereof and method of using the same
SE9904850D0 (en) * 1999-12-30 1999-12-30 Pharmacia & Upjohn Ab Novel process and intermediates
AU2003264502A1 (en) 2002-09-19 2004-04-08 Kaneka Corporation Novel carbonyl reductase, gene thereof and method of using the same
UA89617C2 (en) * 2003-08-18 2010-02-25 Х. Луннбек А/С Succinate and malonate salt of trans 4-(1r,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and use thereof as a medicament
US7772240B2 (en) 2003-08-18 2010-08-10 H. Lundbeck A/S Trans-1(6-chloro-3-phenylindan-1-yl)-3,3-dimethylpiperazine
ES2317277T3 (en) 2004-08-06 2009-04-16 Kaneka Corporation NEW CARBONIL REDUCTASA, GEN THAT CODIFIES AND METHOD OF USE OF THE SAME.
WO2006033333A1 (en) 2004-09-24 2006-03-30 Kaneka Corporation Method of producing aldonic acids and aldose dehydrogenase
WO2006046455A1 (en) 2004-10-27 2006-05-04 Kaneka Corporation Novel carbonyl reductase, gene therefor and use thereof
TWI453198B (en) 2005-02-16 2014-09-21 Lundbeck & Co As H Process for making the trans-1-( (1r , 3s)- 6-chloro - 3 -phenylindan-1- yl ) - 3 , 3 - dimethylpiperazine and salts thereof and for making 4 -((1r , 3s )-6- chloro- 3- phenylindan -1- yl )-1, 2 , 2 -trimethylpiperazine and salts thereof
JP2006262767A (en) 2005-03-24 2006-10-05 Kaneka Corp New glucose dehydrogenase
WO2006129628A1 (en) 2005-05-31 2006-12-07 Kaneka Corporation Process for production of optically active 2-substituted propanal derivative
WO2007099764A1 (en) 2006-02-28 2007-09-07 Kaneka Corporation Novel carbonyl reductase, gene for the reductase, and method for production of optically active alcohol using the reductase or the gene
WO2007099994A1 (en) 2006-03-02 2007-09-07 Kaneka Corporation Novel carbonyl reductase, gene for the reductase, vector, transformant, and method for production of optically active alcohol utilizing these materials
ATE529507T1 (en) 2006-03-31 2011-11-15 Kaneka Corp METHOD FOR PRODUCING ERYTHRO- OR THREO-2-AMINO-3-HYDROXYPROPIONIC ACID ESTERS, NOVEL CARBONYL REDUCTASE, REDUCTASE GENE, VECTOR, TRANSFORMANT AND METHOD FOR PRODUCING OPTICALLY ACTIVE ALCOHOL USING SAME
WO2008066018A1 (en) 2006-11-29 2008-06-05 Kaneka Corporation Novel alcohol dehydrogenase, gene for the alcohol dehydrogenase, vector, transformant, and method for production of optically active alcohol by using them
WO2009036275A1 (en) * 2007-09-13 2009-03-19 Link Medicine Corporation Treatment of neurodegenerative diseases using indatraline analogs
US9303280B2 (en) 2007-09-26 2016-04-05 Kaneka Corporation DNA coding for a novel glucose dehydrogenase
JP2010130912A (en) 2008-12-02 2010-06-17 Kaneka Corp Method for producing optically active 3-quinuclidinol

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
JAMES F. FREEMAN ET AL.: "3-Phenylindones. I. The synthesis of 6-chloro-3-(p-chlorophenyl)-1-indenone and some related compounds", J. AM. CHEM. SOC., vol. 72, 1950, pages 1522 - 1526, XP002721657 *
S.C. PAKRASHI ET AL.: "The Reformatsky reaction on 1-naphthyl-2-bromophenyl ketone", TETRAHEDRON, vol. 18, 1962, pages 1243 - 1249, XP002721656 *
See also references of WO2012063843A1 *

Also Published As

Publication number Publication date
EP2639216B1 (en) 2018-07-11
WO2012063843A1 (en) 2012-05-18
JP2016074712A (en) 2016-05-12
CN103209949B (en) 2016-08-10
CN103209949A (en) 2013-07-17
CN104496780A (en) 2015-04-08
JP6093427B2 (en) 2017-03-08
DK2639216T3 (en) 2018-09-24
JP5941410B2 (en) 2016-06-29
JPWO2012063843A1 (en) 2014-05-12
EP2639216A1 (en) 2013-09-18

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